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WO2007004077A3 - Procede de preparation de tamsulosine - Google Patents

Procede de preparation de tamsulosine Download PDF

Info

Publication number
WO2007004077A3
WO2007004077A3 PCT/IB2006/002654 IB2006002654W WO2007004077A3 WO 2007004077 A3 WO2007004077 A3 WO 2007004077A3 IB 2006002654 W IB2006002654 W IB 2006002654W WO 2007004077 A3 WO2007004077 A3 WO 2007004077A3
Authority
WO
WIPO (PCT)
Prior art keywords
tamsulosin
phosphite
methoxybenzenesulfonamide
ethoxyphenoxy
aminopropyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/IB2006/002654
Other languages
English (en)
Other versions
WO2007004077A2 (fr
Inventor
Taya Jose Espinos
Pedemonte Ignasi Auquer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Medichem SA
Original Assignee
Medichem SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Medichem SA filed Critical Medichem SA
Priority to US11/913,652 priority Critical patent/US20080262089A1/en
Priority to CA002607809A priority patent/CA2607809A1/fr
Priority to EP06808890A priority patent/EP1885692A2/fr
Publication of WO2007004077A2 publication Critical patent/WO2007004077A2/fr
Publication of WO2007004077A3 publication Critical patent/WO2007004077A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne un procédé amélioré de production de tamsulosine qui consiste à faire réagir du 5-(2-aminopropyl)-2-méthoxybenzènesulfonamide avec du 2-(o-éthoxyphénoxy)éthyl bromure dans un solvant phosphite organique afin d'obtenir de la tamsulosine. Du (R)-5-(2-aminopropyl)-2-méthoxybenzènesulfonamide optiquement pur peut être utilisé afin d'obtenir un produit (R)-tamsulosine optiquement pur. Le solvant phosphite organique utilisé dans la réaction peut comprendre des tri-alkyl phosphites de type triéthyl phosphite, triméthyl phosphite, et tributyl phosphite. L'invention concerne en outre des procédés de production de tamsulosine présentant une faible concentration en sous-produits contaminants, de type 5-((R)-2- {Bis-[2-(2-éthoxyphénoxy)éthyl]amino}-propyl)-2-méthoxybenzènesulfonamide, et l'utilisation de ces sous-produits pour contrôler la pureté chimique de la tamsulosine.
PCT/IB2006/002654 2005-05-04 2006-05-04 Procede de preparation de tamsulosine Ceased WO2007004077A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US11/913,652 US20080262089A1 (en) 2005-05-04 2006-05-04 Process for the Preparation of Tamsulosin
CA002607809A CA2607809A1 (fr) 2005-05-04 2006-05-04 Procede de preparation de tamsulosine
EP06808890A EP1885692A2 (fr) 2005-05-04 2006-05-04 Procede de preparation de tamsulosine

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US67733905P 2005-05-04 2005-05-04
US60/677,339 2005-05-04

Publications (2)

Publication Number Publication Date
WO2007004077A2 WO2007004077A2 (fr) 2007-01-11
WO2007004077A3 true WO2007004077A3 (fr) 2007-03-29

Family

ID=37496673

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2006/002654 Ceased WO2007004077A2 (fr) 2005-05-04 2006-05-04 Procede de preparation de tamsulosine

Country Status (5)

Country Link
US (1) US20080262089A1 (fr)
EP (1) EP1885692A2 (fr)
AR (1) AR057290A1 (fr)
CA (1) CA2607809A1 (fr)
WO (1) WO2007004077A2 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101410369A (zh) * 2005-10-28 2009-04-15 麦迪凯姆股份公司 用于制备坦索罗辛及相关化合物的方法
CN102898336B (zh) * 2012-10-16 2013-11-27 北京悦康科创医药科技有限公司 一种盐酸坦索罗辛的制备方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4731478A (en) * 1980-02-08 1988-03-15 Yamanouchi Pharmaceutical Co., Ltd. Sulfamoyl-substituted phenethylamine derivatives, their preparation, and pharmaceutical compositions, containing them
EP0838448A1 (fr) * 1996-10-23 1998-04-29 Dsm N.V. Procédé pour la séparation d'un mélange d'énantiomères
WO2004058694A1 (fr) * 2002-12-26 2004-07-15 Cadila Healthcare Limited Procede de preparation de (r) ou (s)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide enantiomeriquement pur
WO2005063702A1 (fr) * 2003-12-29 2005-07-14 Lek Pharmaceuticals D.D. Preparation de r-5-(2-(2-ethoxyphenoxyetylamino)propyl)-2- methoxybenzenesulphonamide chlorhydrate a purete chimique elevee
JP2006232757A (ja) * 2005-02-25 2006-09-07 Ohara Yakuhin Kogyo Kk フェノキシエチルハライド及びその誘導体の製造法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USH2154H1 (en) * 2003-10-08 2006-04-04 Farmak, A.S. Process for preparing R- and S-isomers of (R)-5-(2-( (2-(2-ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4731478A (en) * 1980-02-08 1988-03-15 Yamanouchi Pharmaceutical Co., Ltd. Sulfamoyl-substituted phenethylamine derivatives, their preparation, and pharmaceutical compositions, containing them
EP0838448A1 (fr) * 1996-10-23 1998-04-29 Dsm N.V. Procédé pour la séparation d'un mélange d'énantiomères
WO2004058694A1 (fr) * 2002-12-26 2004-07-15 Cadila Healthcare Limited Procede de preparation de (r) ou (s)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide enantiomeriquement pur
WO2005063702A1 (fr) * 2003-12-29 2005-07-14 Lek Pharmaceuticals D.D. Preparation de r-5-(2-(2-ethoxyphenoxyetylamino)propyl)-2- methoxybenzenesulphonamide chlorhydrate a purete chimique elevee
JP2006232757A (ja) * 2005-02-25 2006-09-07 Ohara Yakuhin Kogyo Kk フェノキシエチルハライド及びその誘導体の製造法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHANG J-W ET AL: "ENANTIOSELECTIVE SYNTHESIS OF ALPHA-HYDROXY ACIDS EMPLOYING (1S)-(+)-N,N-DIISOPROPYL-10-CAMPHORSULFONAMIDE AS CHIRAL AUXILIARY", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 1, no. 13, 1999, pages 2061 - 2063, XP002926679, ISSN: 1523-7060 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; TAKAOKA, SHIGEKI: "Preparation of phenoxyethyl halides from phenoxyethanols and preparation of tamsulosin from the halides", XP002411565, retrieved from STN Database accession no. 145:314649 *

Also Published As

Publication number Publication date
EP1885692A2 (fr) 2008-02-13
US20080262089A1 (en) 2008-10-23
AR057290A1 (es) 2007-11-28
CA2607809A1 (fr) 2007-01-11
WO2007004077A2 (fr) 2007-01-11

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